The present invention relates to a method for preparing perfluorinated, heterocyclically substituted cycloalkyl compounds and mixtures thereof with corresponding n-alkyl compounds starting from corresponding unfluorinated cycloalkenyl compounds. The present invention further relates to new perfluorinated compounds prepared for the first time by the method of the invention, and to the use of these new compounds.
The compounds which can be prepared in accordance with the invention are of the so-called perfluorocarbon type. Perfluorocarbons are perfluorinated organic carbons which are liquid to waxy at room temperature under standard pressure. They are water-insoluble, biologically inert compounds which consist of carbon and fluorine, and in some cases may also contain hetero atoms such as nitrogen or oxygen. Such compounds are disclosed, for example, in published European Patent Application Nos. EP 77,114; EP 99,652; and EP 151,697. The perfluorocarbon molecules are outstandingly shielded by a uniform shell of fluorine atoms. Therefore, perfluorocarbons are extraordinarily inert chemically and physiologically, and thus nontoxic. Due to their extremely low intermolecular forces, perfluorocarbons have low boiling points in proportion to their molecular weights, and an extraordinarily low surface tension. The very weak intermolecular forces also are responsible for the ability of the perfluorocarbons to dissolve large amounts of gases such as oxygen and carbon dioxide. Due to these properties, especially the ability to physically dissolve and transport oxygen, perfluorocarbons have been used in medicine for preparing oxygen-transporting aqueous emulsions of perfluorocarbons, which are used, for example, as blood substitutes or perfusion media. Further, perfluorocarbons are also suitable for use in other technical fields in which nontoxic and chemically inert liquid or waxy substances are needed, or in which inert substances with the ability to dissolve gases are needed.
Previously known methods for preparing perfluorinated, heterocyclically substituted cycloalkyl compounds start from corresponding saturated, unfluorinated cycloalkyl compounds which must be obtained by complex preparation methods. In comparison with such processes, the method of the invention has the advantage that it uses starting materials which are easily accessible through a small number of reaction steps.